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Vacation Rentals in Kailua, HI

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From
$126
Per Night
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1 / 16
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1 Bedroom, 1 Bathroom, Sleeps 2
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$125
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 4
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$325
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1 / 22
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7 Bedrooms, 2 Bathrooms, Sleeps 8
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$395
Per Night
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1 / 16
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3 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • TV
  • Stove
  • Parking
  • Refrigerator
  • Washer
  • Dishwasher
  • DVD Player
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Beautiful, licensed, newly remodeled 3 Bedrm, 3 Bath Kailua Beach side villa, surrounded with lush tropical gardens, on private estate with swimming pool and jacuzzi.. Just walk down a private beach lane and in less than 2 minutes you would be at the most beautiful beach in the country! It is a... View all property information
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5 of 5 stars Reviewed April 19, 2014
We wanted to celebrate a 50 year anniversary with the whole family and this proved to be the perfect setting! Each family of 4 had their own 'home': one was in Kukui House...
4 of 5 stars Reviewed November 21, 2013
After 5 weeks travelling in the continental US and Canada with 4 children, we thoroughly enjoyed our week at Kukui House Kailua where we could kick back and relax, enjoy day...
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From
$695
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1 / 26
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3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (22) Make Inquiry
Amenities & Details
  • Dryer
  • Dishwasher
  • Deck
  • Refrigerator
  • Microwave
  • Ceiling Fans
  • Stove
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This gorgeous, beautifully furnished Ocean View home is a stone's throw from Kailua Beach and sleeps up to 8 comfortably. There is a large, sparkling, fully tiled swimming pool, 2 jacuzzi tubs, central air conditioning, 3 large bedrooms with ocean views, and 4 baths. Dolphin Manor is an... View all property information
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5 of 5 stars Reviewed August 25, 2014
This is a lovely and comfortable home, just steps from Kailua Beach, that will give any traveler a wonderful taste of Hawaii. We walked the beach every morning, spent time in the...
5 of 5 stars Reviewed July 7, 2014
We rented the house for a family vacation and to attend our son's wedding wedding. It was everything we could of wanted. No surprises and in excellent condition. Great location...
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From
$1,200
Per Night
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1 / 27
4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Stereo System
  • Satellite TV
  • Dryer
  • Washer
  • Dishwasher
  • TV
  • Ceiling Fans
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Maluhia is located just steps away from the white sandy shores of Kailua Beach. The small town of Kailua is busting with popular restaurants and boutiques, and just a short 5 minute drive or 15 minute bike ride away. Kailua is home to world famous Lanikai Beach. The two Mokulua islands are... View all property information
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From
$265
Per Night
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1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Fax
  • TV
  • Washer
  • Hot Tub
  • Stereo System
  • Ceiling Fans
  • Dryer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Charming and Newly remodeled 2 Bedroom, 2 Bath Villa on private Beachside Estate with swimming pool and jacuzii. Just a short 2 minute walk to Kailua Beach through the park. Sleeps 4. View all property information
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4 of 5 stars Reviewed December 11, 2014
This was a great little find for our friends retreat. The only drawback was we had to walk through one bedroom to get to the other. Seeings as we were all friends it wasn't an...
3 of 5 stars Reviewed July 14, 2014
First of all, the hosts are friendly and helpful. The location of the villa is very convenient to Kailua Beach. There is also a communal washer and dryer which is very handy to...
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From
$290
Per Night
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1 / 10
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3 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Aloha and welcome to this comfortable three bedroom one bath house. There is a large back deck with a hot tub. This vacation home sleeps 6 - 7, it has one new Sealy Posturepedic queen size bed, one new Sealy Posturepedic king and two twin size beds, with a sleeper sofa in the living room. This... View all property information
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From
$750
Per Night
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1 / 28
6 Bedrooms, 6 Bathrooms, Sleeps 14
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Amenities & Details
  • Ceiling Fans
  • DVD Player
  • Linens Provided
  • Air Conditioning
  • Stereo System
  • Satellite TV
  • Deck
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how... View all property information
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From
$300
Per Night
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1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (16) Make Inquiry
Amenities & Details
  • Refrigerator
  • Ceiling Fans
  • Stove
  • Washer
  • DVD Player
  • Grill
  • Parking
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a two bedroom rental unit... View all property information
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4 of 5 stars Reviewed October 20, 2014
This is a well appointed, spacious apartment, very close to the beach. Plenty of space for four adults and one small child. Only real negative, is, apart from a small balcony...
5 of 5 stars Reviewed March 10, 2014
I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
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From
$95
Per Night
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1 / 11
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1 Bedroom, 1 Bathroom, Sleeps 4
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Details Reviews (4) Make Inquiry
Amenities & Details
  • TV
  • Washer
  • Parking
  • Internet Access
  • Satellite TV
  • Dryer
  • Grill
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This is a great 300 sq ft studio only 3 min drive to world famous kailua beach This studio has a cal king bed and a futon that can sleep 4 people 55 in flat screen TV free wi-fi kitchen with everything you need to cook all your meals natural stone shower that is very roomy and a tiled swimming... View all property information
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5 of 5 stars Reviewed January 1, 2015
If you're looking for someplace that is not in the middle of the tourist traps, then this is your place. A nice apartment within 10 minutes from the beaches in Kailua. Close to...
5 of 5 stars Reviewed September 28, 2014
John was an incredible host very resourceful and kind always there whenever my wife or I had a question told us all the good restaurants. Very happy great value, clean, bikes...
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From
$350
Per Night
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1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Refrigerator
  • Stove
  • Patio
  • Microwave
  • Satellite TV
  • Parking
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,... View all property information
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From
$475
Per Night
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1 / 21
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Stove
  • Microwave
  • Parking
  • Patio
  • Washer
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is... View all property information
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From
$450
Per Night
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1 / 10
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Stove
  • Ceiling Fans
  • Refrigerator
  • Internet Access
  • Grill
  • Dryer
  • Washer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It is an easy drive to Sea Life... View all property information
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From
$650
Per Night
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1 / 20
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4 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Welcome to Hawaii. Relax. This home away from home offers an authentic island style experience in Kailua. “Kamaaina” is a style rich in... View all property information
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From
$330
Per Night
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1 / 14
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Parking
  • Air Conditioning
  • Stove
  • Washer
  • Grill
  • TV
  • Microwave
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Makana's Place is a three bedroom, two bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is equivalent to a 4-5 bedroom home. Beautifully decorated with well quality furniture (Koa). Makana's Place features a full kitchen plus... View all property information
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From
$195
Per Night
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1 / 15
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1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Deck
  • Grill
  • TV
  • DVD Player
  • Refrigerator
  • Dryer
  • Washer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice... View all property information
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From
$395
Per Night
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1 / 21
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4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Microwave
  • Dryer
  • Stove
  • TV
  • Grill
  • DVD Player
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hale Maluhia (House of Serenity) is a kama'aiana style home near Kailua Beach. In a quiet Kailua neighborhood, the home is a quick 5 minute, one block walk to the world famous secluded white sand beach. Relax with friends and family in this child-friendly family home. Experience the warm 'old... View all property information
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From
$550
Per Night
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1 / 27
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Grill
  • TV
  • Parking
  • Garage
  • Dishwasher
  • Washer
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This Custom beachside home is steps from beautiful Kailua beach. It features a refreshing cobalt blue pool and spa, as well as, a gas firepit for those evenings by the pool. As it's a custom home it offers an indoor fire place and vaulted ceilings, wood floors, berber carpet and the original art... View all property information
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From
$525
Per Night
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1 / 25
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • DVD Player
  • Patio
  • Dishwasher
  • TV
  • Washer
  • Parking
  • Stove
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Hale Pulelehua “The Butterfly House' has a spacious open feeling inside and out. The large windows front and back allow the trade winds to carry the sweet scent of Hawaiian flowers throughout this home. Take in the enormous private yard beautifully landscaped with many native species of the... View all property information
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From
$450
Per Night
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1 / 31
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3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Stove
  • TV
  • Fireplace
  • Parking
  • Grill
  • Washer
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaiian Paradise, across the street is a short path to Kailua Beach, voted #1 beach in America by Conde Nast Traveler Magazine. A beautiful rather secluded beach far less crowed than most beaches in Hawaii. This private home is a home away from home. This 3 bedroom, 3 Bath property is completely... View all property information
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From
$650
Per Night
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1 / 21
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6 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Garage
  • Microwave
  • Dishwasher
  • Washer
  • Dryer
  • Ceiling Fans
  • Parking
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesnt end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for... View all property information
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From
$900
Per Night
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1 / 2
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5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Grill
  • Refrigerator
  • Microwave
  • Hot Tub
  • Parking
  • Safe
  • TV
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
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From
$935
Per Night
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1 / 6
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Parking
  • Washer
  • TV
  • Stove
  • Grill
  • Patio
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine... View all property information
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From
$345
Per Night
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1 / 10
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (7) Make Inquiry
Amenities & Details
  • Grill
  • Ceiling Fans
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
You will find Serenity here. This is the beachfront cottage you've been searching for.This delightful cottage is found in the middle of stunning Kailua Beach. Casually lounge in the small but cozy living room and be astounded by breathtaking views of the beach. Step out your front door and onto... View all property information
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4 of 5 stars Reviewed August 21, 2013
Our family (children age 11 and 9) stayed here for our summer vacation. The location is about as perfect as you can get. A short walk across the lawn right onto one of the most...
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From
$550
Per Night
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1 / 32
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Washer
  • Refrigerator
  • Stove
  • Garage
  • TV
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Endless Summer Getaway.... the name says it all. This fabulous upgraded three bedroom three bath home boasts pride of ownership along with a feeling of hospitality. As you enter into the home you walk into the living/family room, then straight ahead is the sliding door that leads to the outdoor... View all property information
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From
$139
Per Night
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1 / 8
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Studio, 1 Bathroom, Sleeps 3
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. Complimentary assigned parking on property and laundry... View all property information
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From
$199
Per Night
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1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 2
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Details Reviews (3) Make Inquiry
Amenities & Details
  • Grill
  • Washer
  • Stove
  • Safe
  • Dishwasher
  • Dryer
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-MAKAI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the... View all property information
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4 of 5 stars Reviewed January 15, 2015
This was the first time we had hired a rental property in a another country using trip advisor and it was a pleasant experience. Cheryl (the owner) was very prompt in replying to...
5 of 5 stars Reviewed September 21, 2014
We were a bit apprehensive about being the first renters of this new rental, but took a chance since the location and space seemed ideal. We had a wonderful week staying here...
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From
$199
Per Night
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1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
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Details Reviews (3) Make Inquiry
Amenities & Details
  • Washer
  • Stove
  • DVD Player
  • Safe
  • Ceiling Fans
  • Satellite TV
  • Microwave
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-PALI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the world... View all property information
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5 of 5 stars Reviewed December 18, 2014
This is a rental apartment with the owners living on property. It is nestled into the quiet, private, safe and non-tourist town of Kailua on the western shore. Sure beats paying...
5 of 5 stars Reviewed August 28, 2014
We enjoyed our time in Kailua. The apartment was perfect. We had a lot of space and everything was very clean.
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From
$600
Per Night
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1 / 19
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Guest Count
  • Internet Access
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
A cozy and sweet home, Ehu Kai blends a beach cottage feel with luxury. Named for the sea sprays that can be felt from this exceptional property, Ehu Kai is a tranquil retreat, perfect for unwinding from mainland stress. Located at the foot of Kailua Beach, you can escape to total bliss. From the... View all property information
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From
$150
Per Night
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1 / 18
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1 Bedroom, 1 Bathroom, Sleeps 4
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Details Reviews (10) Make Inquiry
Amenities & Details
  • Grill
  • Patio
  • Satellite TV
  • VCR
  • Microwave
  • TV
  • Wi-Fi
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
A private 400 sq foot studio w/fenced courtyard/lanai, in quiet Kaimalino. Relax outdoors or indoors w/full kitchen, bath, cable and internet connections. A short walk will take you to a turtle nesting grounds, the open ocean facing Maui and Lanai islands, sandy Kailua Beach, and Aikahi Shopping... View all property information
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5 of 5 stars Reviewed December 31, 2014
We are so pleased with this cottage. The location was perfect for us and Usha was very hospitable. Kailua's beaches are seriously some of the most beautiful and quiet. Plenty of...
4 of 5 stars Reviewed August 13, 2014
This studio was exactly as advertised and more. It was an easy walk to a beautiful sunrise, supermarkets and restaurants but out of the way enough to avoid the traffic and noise...
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From
$425
Per Night
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1 / 16
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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Details Reviews (2) Make Inquiry
Amenities & Details
  • Dryer
  • Microwave
  • Patio
  • Parking
  • Ceiling Fans
  • Satellite TV
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Experience Hawaii at it's fullest by staying at this amazing 1926 bungalow located between two of the most beautiful beaches in the world. Lanikai and Kailua beaches are just 200 yards away. Kayak, Bicycle, Surfboard, Paddle board and Snorkel Rentals are 200 yards away at Kailua Beach Park. A... View all property information
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5 of 5 stars Reviewed July 18, 2014
We had two families totaling 4 adults and 5 kids stay at this house, and had a fabulous time! The house is beautiful, and set right between two lovely beaches. The house is not...
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From
$150
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
If you're looking for a perfect spot to call home during your stay in Kailua, you'll love this one bedroom/one bath apartment in walking distance of world-famous Kailua and Lanikai Beaches. This unit, which has just been made available as a monthly vacation rental, is tucked away in a quiet,... View all property information
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From
$149
Per Night
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Studio, 1 Bathroom, Sleeps 5
Bookings
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Amenities & Details
  • Grill
  • Ceiling Fans
  • Stereo System
  • DVD Player
  • Porch
  • Safe
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Spacious Studio with Private Entrance & Bathroom This beautiful studio is located in a quiet neighborhood close to world famous Kailua Beach. Property is on the water with a large swimming pool. The area is surrounded by lush tropical Gardens that offer many private seating areas for morning... View all property information
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From
$475
Per Night
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1 / 14
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Ceiling Fans
  • Guest Count
  • Grill
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy the charm of Kailua beach in this delightful kama'aina three bedroom home. Just one house back from the sands of Kailua beach on a private loop, this charming Hawaiiana beach house is a tropical oasis. Three wonderfully appointed bedrooms, a modern kitchen, and spacious, beautifully furnished... View all property information
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5 of 5 stars Reviewed August 17, 2014
We stayed here for 7 nights during June of this year. The house was exactly what we were looking for. The location is ideal as it is not more than 1 minute walk from the beach...
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From
$425
Per Night
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • TV
  • Stove
  • DVD Player
  • Parking
  • Washer
  • Grill
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaiian Style Home, Pool, Tropical Setting, 4 Bdrm, 2 Bath, Short Walk To The Beach, Sparkeling Pool, Lush Tropical Yard Hale Pulelehua “The Butterfly House' has a spacious open feeling inside and out. The large windows front and back allow the trade winds to carry the sweet scent of Hawaiian... View all property information
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From
$225
Per Night
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1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Nearest Beach: 0.0...
  • Number Of Bedrooms
  • HNL: 19.9 mi
  • Living Room Seats...
  • Dining Seats (8)
  • Air Conditioning
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beautiful Single Family Home is sought after neighborhood in Kailua. 15 minutes walk to the beach, Fully furnished with dishes, linens, kitchenware - everything you need. Accommodates 4-6 Some standout features are -- -- 2270 sq feet of house plus a yard that is about 1800 sq feet. -- beautiful... View all property information
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From
$199
Per Night
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1 / 17
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1 Bedroom, 1 Bathroom, Sleeps 3
Booking
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Amenities & Details
  • Stove
  • Wi-Fi
  • Internet Access
  • Ceiling Fans
  • Dryer
  • Microwave
  • Mountain Views
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Completely Renovated Cottage in Kailua in very close walking distance to the beach. High Speed Internet with WiFi Access, HD-TV, Oven, Microwave, Toaster, Coffee Maker, Refrigerator, Washer, Dryer, Bathtub. Eastern King Size Bed and additional sleeper couch for another Queen-Size Bed. Our Cottage... View all property information
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From
$139
Per Night
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1 / 7
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Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Internet Access
  • Ceiling Fans
  • Microwave
  • TV
  • Hairdryer
  • Wi-Fi
  • Air Conditioning
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Walk to Kailua Beach or Town. Located at: 131 Kuulei Road Kailua, Hawaii The Hawaii Sheffield House Ginger Studio is located between Kailua Beach and Kailua Town.The Hawaii Sheffield House has its own 'secret garden with an outdoor dining table. It is a delightful home away from home for... View all property information
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4 of 5 stars Reviewed January 31, 2014
We were surprised just how spacious this studio is and how nice and fresh it is. Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
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From
$500
Per Night
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1 / 30
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Dryer
  • TV
  • Washer
  • Grill
  • Dishwasher
  • Safe
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Aloha and welcome to your beach house. This charming home has everything you need for your dream vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself comfortable. As soon as you walk through the door the stress of everyday life will melt away. Most of the... View all property information
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5 of 5 stars Reviewed November 18, 2014
This was our first visit to Hawaii and we loved every minute of it. The vacation home and owners were wonderful. The house was as described and perfect for our stay. The owners...
4 of 5 stars Reviewed November 17, 2014
When I was shopping for a place to stay in Hawaii, my daughter wanted a house where she could cook her own foodf for the kids and have boogie boards and snorkel gear available for...
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From
$185
Per Night
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1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Grill
  • Parking
  • Washer
  • Patio
  • Dryer
  • Refrigerator
  • Hot Tub
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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5 of 5 stars Reviewed November 9, 2014
My husband and I stayed at Lanikai Love for 10 days for our honeymoon. We absolutely loved every second of our stay here! The property is exactly as described and even more...
3 of 5 stars Reviewed September 20, 2014
Not pravite pool and hot tub, shared with others lived in that house. No late check out option 11:00 too early. Living room got only fan it's kind hot dining there.
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From
$174
Per Night
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1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
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Amenities & Details
  • Parking
  • Grill
  • Air Conditioning
  • Ceiling Fans
  • Hairdryer
  • Refrigerator
  • Outdoor Dining Area
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite has free off street parking, free wifi, cable TV, boogie boards and a first morning... View all property information
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From
$155
Per Night
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Dryer
  • Grill
  • Stove
  • Ceiling Fans
  • Microwave
  • Hot Tub
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$500
Per Night
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1 / 19
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • TV
  • Dishwasher
  • Grill
  • DVD Player
  • Stove
  • Microwave
  • Dryer
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Come experience the beauty and magic of Kailua. Stay in our charming, hawaiiana Hale Nalu Palekaiko, Surf Paradise Hale...See why people call Kailua papalani, heaven on earth. Relax in our comfortable and welcoming hale. The main house has three bedrooms, 2 bathrooms, living, dining and lanai... View all property information
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From
$249
Per Night
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1 / 19
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (6) Make Inquiry
Amenities & Details
  • Internet Access
  • Refrigerator
  • Satellite TV
  • Linens Provided
  • Mountain Views
  • Parking
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This beach-side cabana was newly constructed in 2001 and remains in immaculate condition. Equipped with many amenities, it is located just 100 steps along a private beach access path to the shore of world-famous Kailua Beach. Enjoy the caressing tradewinds on your private lanai - surrounded by... View all property information
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5 of 5 stars Reviewed August 6, 2012
This cabana is in a great location if you are looking for something peaceful and relaxing. We stayed over a weekend after being in Waikiki the week prior, and it was a delightful...
5 of 5 stars Reviewed February 6, 2012
We really enjoyed our short stay at Julie's Cabana. It is beautifully decorated and she made us feel especially welcome with a basket of local goodies and ideas and directions to...
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From
$130
Per Night
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1 / 18
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Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Hot Tub
  • TV
  • Washer
  • Patio
  • Dryer
  • Stove
  • Parking
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning studio. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$330
Per Night
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1 / 19
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3 Bedrooms, 1 Bathroom, Sleeps 7
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Amenities & Details
  • # Of Bathrooms
  • Long Term Rentals...
  • Guest Count
  • House Swap
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Hale Plumeria is the perfect home for your vacation; away from tourist areas, yet convenient to airport & all major attractions such; scenic drive to North Shore, Sea life Park, Lanikai, Kailua Beach, Hiking, snorkeling, paddle boarding, kayaking, surfing, boogie boarding & so much more... Hale... View all property information
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From
$1,000
Per Night
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6 Bedrooms, 4 Bathrooms, Sleeps 15
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Amenities & Details
  • TV
  • Safe
  • Hot Tub
  • Microwave
  • Washer
  • Grill
  • Dishwasher
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit... View all property information
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5 of 5 stars Reviewed July 4, 2012
Stayed one week at this beautiful home. Traveled with 7 adults and 2 teens. Everyone had a room and plenty of space. The home is situated so that breeze flow through out the...
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From
$5,600
Per Week
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8 Bedrooms, 4 Bathrooms, Sleeps 18
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Amenities & Details
  • Garage
  • TV
  • Stove
  • Dishwasher
  • Grill
  • Microwave
  • Refrigerator
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The property is located approx. 10 miles from the city of Honolulu . 15 minutes walk to the nearest beach access. East of the island of Oahu . Surrounded by lush green mountains . The house has tranquil and peaceful atmosphere . This house is fully furnished in an authentic island style. The... View all property information
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4 of 5 stars Reviewed February 19, 2014
On our arrival we were met by Sonya (owner) with cup cakes for the boys. She welcomed us and gave us a tour of her house. House was clean, well decorated, and most of all...
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From
$1,450
Per Night
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1 / 22
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Air Conditioning
  • Terrace
  • TV
  • Parking
  • Grill
  • Ceiling Fans
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This getaway’s name, Maluhia, translates into “Peace” in Hawaiian, and it’s not hard to see why—nestled in the region of Kailua, known for its turquoise waters, and white sandy beaches, you’ll feel relaxed in this tranquil space, it’s one of our top Oahu vacation rentals. The low-key area of Kailua... View all property information
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Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.